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. 2009 Sep 10;52(17):5556-9.
doi: 10.1021/jm900686q.

Influence of the side chain next to C-terminal benzimidazole in opioid pseudopeptides containing the Dmt-Tic pharmacophore

Gianfranco Balboni  1 , Claudio Trapella, Yusuke Sasaki, Akihiro Ambo, Ewa D Marczak, Lawrence H Lazarus, Severo Salvadori
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Influence of the side chain next to C-terminal benzimidazole in opioid pseudopeptides containing the Dmt-Tic pharmacophore

Gianfranco Balboni et al. J Med Chem. .

Abstract

To improve the structure-activity studies of the lead delta opioid agonist H-Dmt-Tic-Asp*-Bid, we synthesized and pharmacologically characterized a series of analogues in which the side chain next to 1H-benzimidazole-2-yl (Bid) was substituted by those endowed with different chemical properties. Interesting results were obtained: (1) only Gly, Ala, and Asp resulted in delta agonism, (2) Phe yielded delta antagonism, (3) and all other residues except Glu (devoid of any activity) gave mu agonism.

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